With a goal of contextualizing teacher job dissatisfaction during the first full school year of the COVID-19 pandemic, we contrast teachers' experiences with the decade and a half leading up to the pandemic. We draw on nationally representative data from the Schools and Staffing Survey and National Teacher and Principal Survey from the 2003-04 to 2020-21 school years. Through descriptive and regression analysis, we show that (1) increases in teacher dissatisfaction beginning in the 2015-16 school year persisted into the 2020-21 school year, (2) levels of dissatisfaction during the pandemic were not equal across subpopulations of teachers, and (3) positive working conditions consistently predicted lower job dissatisfaction, including in the 2020-21 school year.